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HERO ID
1175960
Reference Type
Journal Article
Title
Hydration reactions of phosphorylated 1,3-enynes
Author(s)
Christov, VC; Aladinova, VM; Prodanov, B
Year
1999
Is Peer Reviewed?
1
Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN:
1042-6507
EISSN:
1563-5325
Volume
155
Page Numbers
67-79
DOI
10.1080/10426509908044971
Web of Science Id
WOS:000088788400006
Abstract
Hydration of the 3-alkene-1-ynephosphonic dimethyl esters 3 in the presence of a mixture of mercuric sulfate and sulfuric acid as a catalyst takes place with addition of water to the triple bond and hydrolysis of the phosphonate group with formation of the 2-oxo-3-alkenephosphonic acids 4, Ketalation of the 3-alkene-1-ynephosphonic dimethyl esters 3 with methanol using as a catalyst a mixture of yellow mercuric oxide, trichloroacetic acid and boron trifluoride etherate and subsequent hydrolysis of the prepared phosphorylated ketals B leads to the 2-oxo-3-alkenephosphonic dimethyl esters 5. Treatment of 3 with water in the presence of concentrated hydrochloric acid yields the 3-alkene-1-ynephosphonic acids 6.
Keywords
3-alkene-1-ynephosphonic dimethyl esters; mercuric catalysts; hydration; hydrolysis; 2-oxo-3-alkenephosphonic acids; ketalation; 2-oxo-3-alkenephosphonic dimethyl esters; 3-alkene-1-ynephosphonic acids
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Methanol (Non-Cancer)
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